228 THE ANTIBIOTICS 



Chemical and physical properties: Basic, water-soluble substance. Most 

 stable at pH 3.0-3.5; [af D 5 (hydrochloride) -22°. Similar to strepto- 

 thricin. Can be separated by paper chromatography into two active 

 components, A and B. Streptolin A sulfate has the empirical formula 

 CnH 3 i_33N 6 08 or C24H45N7O11 for the free base. Acid hydrolysis of 

 streptolin indicates that it contains an amino sugar, a basic substance, 

 and an isomer of lysine (isolysine). 



Biological activity: Active against gram-positive and gram-negative bacteria. 



Toxicity: LD (mice), intravenous, about 4.5 mg/kg; LD 10 o, about 13.5 

 mg/kg. 



Utilization: None. 



Reference: Rivett, R. W., and Peterson, W. H., J. Am. Chem. Soc, 69, 

 1947, 3006-3009; Larson, L. M., Sternberg, H. E., Peterson, W. H., 

 Smissman, E. E., Sharpe, R. W., and Tamelen, E. E. van., Abstr. 

 of papers 121 Meeting, Am. Chem. Soc, 1952, p. 8C; J. Am. Chem. 

 Soc, 75, 1953, 2029-2031; ibid., 2036-2039. 



Streptomycin 



Produced by: Streptomyces griseus and S. bikiniensis. 



Synonym: Streptomycin II. 



Method of extraction: Adsorption on activated charcoal and elution with 

 acid alcohol. Adsorption on IRC 50 and elution with dilute HC1. 



Chemical and physical properties: Basic, white, stable substance. Water- 

 soluble, insoluble in organic solvents. Inactivated by cysteine and hy- 

 droxylamine. Heteroglucoside, composed of an organic base, strepti- 

 dine, and of two sugar moieties forming streptobiosamine. C21H39N7O12. 



Biological activity: Active against gram-positive, gram-negative, and acid- 

 fast bacteria. Not active against fungi, rickettsiae, and viruses. 



Toxicity: LD50 (mice), subcutaneous, 900 mg/kg; intravenous, 200 mg/kg; 

 oral, 9000 mg/kg. Vestibular disturbances are more common with 

 streptomycin than with dihydrostreptomycin . 



Utilization: Treatment of tuberculosis mainly in combination with para- 

 aminosalicylic acid and isoniazid. Treatment of various infections 

 caused by gram-negative and gram-positive bacteria. 



References: Waksman, S. A., Streptomycin, Williams and Wilkins, 1949; 

 Waksman, S. A., Literature on Streptomycin, Rutgers University 

 Press, 1952. 



Streptomycin-Isoniazid Complex 



Produced by: Chemical derivative of streptomycin and isoniazid. 

 Synonym: Streptohydrazid. 



